Wiltshire Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Wiltshire Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at the Palms IV
Price was $2,258, price is now $1,278 per person
$1,278
per person
Jan 19 - Jan 25
found 7 hours ago
Roundtrip non-stop flight included
Louisville (SDF) to Montego Bay (MBJ)
Book a stay at this golf villa in St. Ann's Bay. Enjoy free WiFi, free parking, and a golf course. Popular attractions Cranbrook Flower Forest and Priory Beach are located nearby.
We were greeted by Ms Kathy who took us on a tour of the villa. It was very nice and more than enough space for me and my 4 girls. The pool/clubhouse was very very nice. I was very skeptical of doing this online and this place did not disappoint. I will be returning! Big ups to Kathy!!!
Reviewed on Mar 23, 2018
Iberostar Selection Rose Hall Suites - All Inclusive
Northern Estates
Price was $4,606, price is now $2,271 per person
$2,271
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Montego Bay (MBJ)
Book a stay at this luxury resort in Montego Bay. Enjoy free breakfast, free WiFi, and 4 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rose Hall Great House and Greenwood Great House are located nearby.
Hotel Riu Montego Bay - Adults Only - All Inclusive
Save 100% on your flight
Price was $2,860, price is now $1,454 per person
$1,454
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby.
Iberostar Waves Rose Hall Beach - All Inclusive
Northern Estates
Price was $3,681, price is now $1,876 per person
$1,876
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Montego Bay (MBJ)
Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rose Hall Great House and Greenwood Great House are located nearby.
I wouldn’t recommend. The hotel is confusing and the isn’t clean.
Reviewed on Nov 6, 2026
Hotel Riu Palace Aquarelle - All Inclusive
Falmouth Historic Town Centre
Save 100% on your flight
Price was $2,671, price is now $1,377 per person
$1,377
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
Book a stay at this beach hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Water Square and Martha Brae River are located nearby.
Everything about this resort is incredible! Clean, food is great, and the staff goes above and beyond for their guest! Loved it so much we plan on going back in a few months!
Reviewed on Nov 7, 2026
Excellence Oyster Bay - Adults Only All Inclusive
Save 100% on your flight
Price was $3,884, price is now $2,183 per person
$2,183
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Luminous Lagoon and Water Square are located nearby.
Top Hotel Deals
Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore Montego Bay Saint James
12.66 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and ...
Coyaba Beach Resort
18 Mahoe Bay, Ironshore Montego Bay St. James Parish
13.57 km from city center
Stay at this hotel in Montego Bay. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Rose Hall Great House and Doctor's Cave Beach are located ...
Hotel Riu Reggae - Adults Only - All Inclusive
Montego Bay Montego Bay
12.44 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and ...
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
7.95 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Doctor's Cave ...
Grand Palladium Jamaica Resort & Spa All Inclusive
The Point Lucea Hanover
22.85 km from city center
Book a stay at this luxury resort in Lucea. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
SeaGarden Beach Resort - All Inclusive
8 Kent Avenue Montego Bay Saint James
8.71 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach ...
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
7 Jimmy Cliff Blvd Montego Bay Saint James
8.05 km from city center
Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach ...
Hotel 39 Jamaica
39 Jimmy Cliff Boulevard Montego Bay
7.51 km from city center
Book a stay at this luxury hotel in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Toby's Resort
1 Kent Avenue Montego Bay Saint James
8.4 km from city center
Stay at this hotel in Montego Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. ...
Iberostar Waves Rose Hall Beach - All Inclusive
Rose Hall Beach Main Road Montego Bay Saint James
20.89 km from city center
Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rose Hall Great ...
Hotel Grand A View
3 RAMPARTS CLOSE Montego Bay ST JAMES
8.15 km from city center
Stay at this hotel in Montego Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hotel Riu Palace Jamaica - Adults Only - All Inclusive
Mahoe Bay - Ironshore P O Montego Bay Saint James
12.57 km from city center
Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach ...
Iberostar Selection Rose Hall Suites - All Inclusive
Rose Hall Main Road Montego Bay Saint James
21.03 km from city center
Book a stay at this luxury resort in Montego Bay. Enjoy free breakfast, free WiFi, and 4 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Jan 11 - Thu, Jan 14
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$327 Roundtrip, found 4 days ago
$327
Roundtrip
found 4 days ago
Mon, Nov 9 - Thu, Nov 12
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$358 Roundtrip, found 5 days ago
$358
Roundtrip
found 5 days ago
Wed, Feb 24 - Mon, Mar 1
FLL
Fort Lauderdale - Hollywood Intl.
MBJ
Sir Donald Sangster Intl.
$394 Roundtrip, found 1 day ago
$394
Roundtrip
found 1 day ago
Fri, Nov 20 - Sun, Dec 6
EWR
Newark Liberty Intl. Airport
MBJ
Sir Donald Sangster Intl.
$403 Roundtrip, found 5 days ago
$403
Roundtrip
found 5 days ago
Mon, Dec 7 - Fri, Dec 18
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$421 Roundtrip, found 3 hours ago
$421
Roundtrip
found 3 hours ago